1L-(1,2,5/3,4)-2,3,4-tri-O-benzyl-1-C-benzyloxymethyl-1,2,3,4,5-cyclohexanepentol

Base Information

• Chemical Name: 1L-(1,2,5/3,4)-2,3,4-tri-O-benzyl-1-C-benzyloxymethyl-1,2,3,4,5-cyclohexanepentol
• CAS No.: 307529-51-7
• Molecular Formula: C₃₅H₃₈O₆
• Molecular Weight: 554.683

Synonyms:1L-(1,2,5/3,4)-2,3,4-tri-O-benzyl-1-C-benzyloxymethyl-1,2,3,4,5-cyclohexanepentol

Chemical Property of 1L-(1,2,5/3,4)-2,3,4-tri-O-benzyl-1-C-benzyloxymethyl-1,2,3,4,5-cyclohexanepentol

Chemical Property:

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Technology Process of 1L-(1,2,5/3,4)-2,3,4-tri-O-benzyl-1-C-benzyloxymethyl-1,2,3,4,5-cyclohexanepentol

There total 3 articles about 1L-(1,2,5/3,4)-2,3,4-tri-O-benzyl-1-C-benzyloxymethyl-1,2,3,4,5-cyclohexanepentol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 44.0%

2L-(2,3/4,5)-2,3,4-tri-O-benzyl-5-C-benzyloxymethyl-2,3,4,5-tetrahydroxycyclohexanone (306968-48-9) → 1L-(1,2,5/3,4)-2,3,4-tri-O-benzyl-1-C-benzyloxymethyl-1,2,3,4,5-cyclohexanepentol (307529-51-7) + 1L-(1,2/3,4,5)-2,3,4-tri-O-benzyl-1-C-benzyloxymethyl-1,2,3,4,5-cyclohexanepentol

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; at -10 ℃; for 0.5h;

DOI:10.1016/S0040-4020(00)00621-9

Reference yield:

3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-hydroxy-2,2-dimethylpropyl)-D-manno-hept-1-enitol (306968-47-8) → 1L-(1,2,5/3,4)-2,3,4-tri-O-benzyl-1-C-benzyloxymethyl-1,2,3,4,5-cyclohexanepentol (307529-51-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 93 percent / triethylamine; 4-(dimethylamino)pyridine / dimethylformamide / 2 h / 20 °C

2.1: dimethyl sulfoxide; acetic anhydride / 20 °C

2.2: ZnCl₂ / tetrahydrofuran; H₂O / Heating

3.1: 44 percent / sodium borohydride / methanol; tetrahydrofuran / 0.5 h / -10 °C

With dmap; sodium tetrahydroborate; acetic anhydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(00)00621-9

Reference yield:

3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-tert-butyldimethylsilyloxy-2,2-dimethylpropyl)-D-manno-hept-1-enitol (306968-50-3) → 1L-(1,2,5/3,4)-2,3,4-tri-O-benzyl-1-C-benzyloxymethyl-1,2,3,4,5-cyclohexanepentol (307529-51-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dimethyl sulfoxide; acetic anhydride / 20 °C

1.2: ZnCl₂ / tetrahydrofuran; H₂O / Heating

2.1: 44 percent / sodium borohydride / methanol; tetrahydrofuran / 0.5 h / -10 °C

With sodium tetrahydroborate; acetic anhydride; dimethyl sulfoxide; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4020(00)00621-9

upstream raw materials:

2L-(2,3/4,5)-2,3,4-tri-O-benzyl-5-C-benzyloxymethyl-2,3,4,5-tetrahydroxycyclohexanone

3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-hydroxy-2,2-dimethylpropyl)-D-manno-hept-1-enitol

3,4,5,7-tetra-O-benzyl-1-deoxy-2-O-(3-tert-butyldimethylsilyloxy-2,2-dimethylpropyl)-D-manno-hept-1-enitol

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